1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22633544, compound

HRID 2416947Notes

Reaction equation

HRID 2416947 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=O.[CH:34]([C:37]1[CH:43]=[CH:42][CH:41]=[C:40]([CH:44]([CH3:46])[CH3:45])[C:38]=1[NH2:39])([CH3:36])[CH3:35]>CN(C=O)C>[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([NH:39][C:38]1[C:40]([CH:44]([CH3:45])[CH3:46])=[CH:41][CH:42]=[CH:43][C:37]=1[CH:34]([CH3:36])[CH3:35])=[O:33]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 32484DiisopropylanilineHCID 757711-HydroxybenzotriazoleHCID 5482219-Bromononanoic Acid

Product 1

HCID 22633544HCID 22633544, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

WSC ( 809 mg, 4.6 mmols) and HOBt (621 mg, 4.6 mmols) were added to a DMF (20 ml) solution of the resulting carboxylic acid (1.19 g, 5 mmols) and 2,6-diisopropylaniline (738 mg, 4.2 mmols), and stirred at room temperature for 12 hours. The reaction mixture was extracted with ether. The organic layer was washed with water, 1 N HCl, an aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate, and the solvent was evaporated. Then, the residue was purified through silica gel column chromatography (developer:hexane/acetone=5/1), and the resulting crystals were recrystallized from ether-hexane to obtain 666 mg (yield: 34%) of 9-bromo-N-(2,6-diisopropylphenyl)nonanamide as colorless needle-like crystals.

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. washThe organic layer was washed with water, 1 N HCl
  3. dry with materialan aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThen, the residue was purified through silica gel column chromatography (developer:hexane/acetone=5/1)
  6. customthe resulting crystals were recrystallized from ether-hexane

Sources & evidence

ORD record
ord-f8e8ba3ed3e44179aa8c5d7aede76e10
Source dataset
uspto-grants-2004_11
Patent number
US06825223B2

Reaction notes

Loading…